Fire Island Pines Holidays

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Top hotels in Fire Island Pines

The Pines Men-Only Stay

The Pines Men-Only Stay

488 Tarpon Walk Sayville NY
Rp5.218.200
Rp5.961.793 total
26 Aug - 27 Aug
includes taxes & fees
10/10 Exceptional! (5 reviews)
"This is a gem... Can only recommend it , if you are looking for the best stay in the Pines. Love Andrey and the team."

Reviewed on 8 Aug 2026

The Pines Men-Only Stay
The Madison Fire Island Pines

The Madison Fire Island Pines

22 Atlantic Walk Sayville NY
The Madison Fire Island Pines
 Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2050 Express Dr S Hauppauge NY
Fully refundableReserve now, pay when you stay
Rp2.783.040
Rp3.179.622 total
17 Sept - 18 Sept
includes taxes & fees
8.2/10 Very good! (1,551 reviews)
"Room 218 close by stairwell exit. Door does not close quietly and was constantly slamming from hotel guests"

Reviewed on 20 Aug 2026

Holiday Inn Express Hauppauge-Long Island
See all 718 properties in Fire Island Pines
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Fire Island Pines attractions

Carrington House

10.0/10 (1 review)
This historic 1912 bungalow was where Truman Capote wrote "Breakfast at Tiffany's" while hosted by Frank Carrington. Tours reveal its significance as a cultural hub for artists and the LGBTQ+ community.
See properties

What to do in Fire Island Pines

Long Island: Yacht Charters, Location: Port Jefferson Harbor

Long Island: Yacht Charters, Location: Port Jefferson Harbor

Rp27.097.500
per traveller
Long Island: Yacht Charters, Location: Port Jefferson Harbor
See all activities in Fire Island Pines

Frequently asked questions

How much does a Fire Island Pines holiday package cost?
You'll find cheap prices on Expedia for your Fire Island Pines break. However, factors like the hotel choice, length of stay and season will influence how much your holiday to Fire Island Pines costs.
What are the cheapest months to go to Fire Island Pines?
To score cheap Fire Island Pines holiday packages, plan your trip outside of busy periods like public holidays and major festivals. You'll generally find better availability and lower prices for flights and hotels.
How many days is enough for Fire Island Pines?
Generally, a handful of days is enough to check out the main sights during your Fire Island Pines holiday. However, if you prefer to have more time to rest or take day tours, think about extending your itinerary.
How to find the best Fire Island Pines package deals?
Use Expedia's handy filters to help you find some tempting Fire Island Pines package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Fire Island Pines package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Fire Island Pines holiday as a package?
You can enjoy significant savings on your Fire Island Pines escape by booking a tailored holiday package. Check the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Fire Island Pines?
If you're planning a spur-of-the-moment Fire Island Pines adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Fire Island Pines?
  1. Choose your dates: The things you'd like to do in Fire Island Pines and your favourite season will help you decide when to get away.
  2. Set a budget: Consider costs like transportation, flights and meals when calculating how much to put aside for your trip to Fire Island Pines. Then, pick a property that fits your budget, whether that's a low-cost option or a more upscale getaway.
  3. Decide how long to go for: Now that you're more familiar with Fire Island Pines, you can work out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodation: After you've nailed down your dates and duration, lock in the perfect Fire Island Pines holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.